Escaping to Chicago for a Hamilton Weekend with My Mom

Written byKristin

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Let’s talk about how my mom is impossible to surprise. I’m sure you know the type: always thinking of others, selfless to a fault, doesn’t worry about her own self-care, but needs a break—particularly after eight months of full-time childcare of my niece. So back in May, I posed an idea to my sister: Let’s take my mom on a surprise Hamilton weekend in Chicago.

You see, around that time, my Nashville friends were flocking to Chicago in droves. Not only is it cheap and easy to get there (thanks, Southwest!), but the opening of Hamilton at Chicago’s CBIC Theatre meant that suddenly tickets were available to the masses. And not at the $1000 price tag you see in New York, but at the much more reasonable price of $200 a seat, which may not sound like a bargain but is what you typically pay to see a Broadway show.

So I started doing my research and realized I could get tickets for pretty much any show in September or October that I wanted. Only, my sister wouldn’t be joining us (see: she’d have no childcare with my mom away), so I did my due diligence and booked our flights for when airfare was lowest and hotels were astronomically expensive (doh). All that was left to do was wait and surprise her on her birthday in October.

Only, as previously stated, my mom is impossible to surprise. We’ve had season tickets to Nashville’s traveling Broadway tour series for more than 20 years and were at the very disappointing follow-up to The Phantom of the Opera back in June when the friends seated next to us told Mom all about their recent trip to Chicago to see Hamilton.

“Oh, I can’t wait!” Mom, who already knew every word of the soundtrack by heart, said. “I’m going in just a few weeks!”

To which point I did a double-take, jerked around and screamed “WHAT!” (Luckily, it was during intermission.)

“Oh yeah,” she said. “I bought tickets for July.”

To which I said, “a) with whom? and b) WHEN WERE YOU GOING TO TELL ME?”

Nonchalantly, “oh, I thought I’d take you,” she responded. So then I had to spoil the plan.

Moms, man. IMPOSSIBLE TO SURPRISE.

Nevertheless, it all worked out, just not in the way I hoped. She canceled her July trip and we went together in October as I had originally planned. And she’s going again next week with friends, so really she didn’t miss out. I mean, Hamilton three times in six months would be a bit much, but two is totally manageable (I kid, I kid … and am super jealous!)

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Where to Stay in Chicago

On this particular trip, I cashed in some coveted hotel rewards points to stay at the Langham Chicago. One thing I learned very quickly when searching hotels in Chicago is that they aren’t cheap—not by a long shot. A three-star hotel was $300 a night, and the rooms were tiny. So when I saw I could use points for a room at the five-star Langham for not a lot more per night (around $100 with taxes and fees)—and get a room that was 600 square feet in size—I bit the bullet and did just that.

Our stay at the Langham surpassed expectations. We had phenomenal service from the bellhop who welcomed us at the front entrance, then called up to check-in so they knew we were coming and greeted us by name, to the server who delivered the room service we took full advantage of. (Somehow, the hotel “package” I booked came with $40 F&B credit a day, so obviously we weren’t going to let that go unused.)

The Langham is also centrally situated among the other high-rises in River North. Staying along the riverfront made sense for Mom and me. We were only there for a little over 48 hours and had planned on going full-out tourist, which we are not ashamed to admit. I’d really love to go back with SVV and spend more time there visiting some of the neighborhoods outside of the Loop, as well as diving into Chicago’s robust mural scene. When we do that, I imagine we’ll rent an Airbnb in Logan Square or maybe Lincoln Park, where there are plenty of options for less than $200 a night.

Doing the Tourist Thing

Even though, it was on the cusp of winter, we set out by foot to see some of River North before veering over to Michigan Avenue where Mom wanted to get a little early Christmas shopping in. On my list was the famed flamingo mural that takes up residence on the front of Flamingo Rum Club, which conveniently was only a few blocks from us.

The Chicago tourism office gave us a CityPASS that allowed us admission to certain attractions, and while the iconic Skydeck in the former Sears Tower (now the Willis Tower) was on there, I knew there was no way I’d get my mom to go to the top of that with her severe acrophobia. So I tricked her and took her to 360 CHICAGO at the top of the John Hancock building instead, which was only slightly less terrifying (to her; I’m fine with heights).

I’d read a bit about the Skydeck vs. 360 Chicago debate on my friend Amanda’s blog while trying to decide the best option for Mom and me and was prepared for a bit of a wait; she said it can take up to an hour in busy summer months. But we were in luck, being there on a chilly weekday in October, as not only was there no wait at all, but we had the elevator entirely to ourselves! The ride up is about 40 seconds, and for as scared as Mom is of heights, I’ve got a crippling fear of elevators and getting trapped in one (see: extremely claustrophobic), so the fact that we had it all to ourselves was pretty miraculous.

Even if there had been a wait, however, the CityPASS offers you Express Entry, meaning you get to jump to the front of the line. That said, go in the shoulder season so you’re not bumping into tourists at the top. We never had to wait to take a photo as the crowds were nonexistent, and there was just a small sprinkling of people here and there.

It was an overcast day by the time we got to the top, but that didn’t prohibit us from seeing far. I was proud of Mom for getting past her fears—even if she did spend most of the time not taking in the view, ha! Our Lyft driver had recommended we get a cocktail at the Signature Room on the 95th Floor, but we were seeing Hamilton that night and sadly didn’t have time. I think if you’re not planning on doing 360 CHICAGO, going to the Signature Room is probably a great way to get a similar view.

Because we had exactly 48 hours in Chicago, we didn’t make it to the other attractions the pass offers, which includes Shedd Aquarium (priority entry), Skydeck Chicago (fast pass), Field Museum (VIP entry), and the Adler Planetarium (VIP entry) or Art Institute of Chicago (fast pass), but I’m planning a return in spring and intend to get another CityPASS then (each one expires nine days from first using it). For $106 an adult, this pass is a total steal, particularly when you factor in the priority access you get with it.

And, of course, you can’t go to Chicago without stopping by Millennium Park. Not only is it a gorgeous display of greenery and seasonal foliage right in the heart of the city, but it also boasts one of Chicago’s most recognizable monuments, the Bean, as well as an art museum right in the heart of the park.

The Bean’s real name is The Cloud Gate sculpture, and it was commissioned at the time of the park’s opening in 2004, designed by London-based artist Anish Kapoor. The way it bends and reflects instantly made it one of Chicago’s most photographed spots and a must-see for any tourist.

The park also has a striking amphitheater that mimics its overall artsy feel. There’s a free jazz series, Millennium Park Summer Music Series, held here in summer months, which I imagine is a pretty fun time to chill in this awesome urban sanctuary.

And, for all of you street art lovers, just a few blocks from the Bean is an original Kobra, my favorite street artist out of Brazil, who painted Muddy Waters two years ago at 17 N. State St. as part of the Wabash Arts Corridor project.

Exploring Chicago’s Architecture Scene

On my last trip to Chicago five years ago, I did an architecture tour by foot with the Travel Mindset team. But one thing every last friend I’ve ever known who’s gone to Chicago—architects included—has told me to do is an architecture tour by boat aboard the First Lady. And I’m nothing if not an attentive pupil.

Chicago’s First Lady Cruises partners with the Chicago Architecture Center for this guided trip up the river and back in time. All tours leave from the Chicago Riverwalk at Michigan Avenue and Wacker Drive, and purchasing tickets online in advance is advisable as they often sell out in peak tourist months.

You don’t have to be knowledgable about architecture to enjoy this tour; it’s informative and laced with history about Chicago’s past, though I particularly enjoyed the Art Deco-period and wacky MCM buildings we saw lining parts of the riverfront.

The tour lasts roughly 90 minutes, and as it was chilly at best the day we were out on the water, by the end of it, Mom and I had cozied up in the enclosed interior on the bottom level to sip hot chocolate and warm our numb hands as we ended our loop of the river.

Note: Tours are only given from late-March through late-October due to Chicago’s weather conditions, so you’ll have to wait until spring for the next season to open.

Getting Out of the Loop

On our final day in town, our flight out wasn’t until 9:30pm so we had the entire morning and afternoon ahead of us and high-tailed it out to Logan Square. The purpose was two-fold: to see some cool murals and catch up with my friend John.

We took a Lyft out there, then the L back later in the afternoon. Let’s just say taking the L (aka Chicago’s metro) was a much more enjoyable experience—and far quicker at that—so if you’re near a station, don’t be afraid to hop on the train. The traffic is just too dense and the cabs too jerky for my sensitive stomach’s liking.

Logan Square is along the train line, and as such, there was plenty of public art to be had; graffiti artists were the original muralists and love painting trains and beneath tracks. I always try and see the Greetings Tour postcard murals anytime I’m passing through a participating city, but after waiting 20 minutes—then looping back later with the same corporate group still hogging the space—Mom and I had to pass on our selfie.

Luckily, on our walk from there to Revolution Brewing Co., there was plenty of art—some graffiti, other murals—to be found.

At Revolution Brewing, we met up with John, who was not only my former coworker but also my co-columnist when we wrote a he-said, she-said style dating column. That’s right folks: Yours truly dished out dating advice to UT’s campus-at-large. It’s funny because many (read: 14 years later), I still sometimes get recognized from those days by fellow Vols who were in Knoxville at the same time as me!

Back to the point, though. I saw on social media a few months ago that John had switched jobs from working as a writer for a dermatology association to manning communications for Revolution Brewing. I’d say, he’s in a gig much better-suited for him being the beard-sporting, beer-loving dude that he is. We met up with him at Revolution’s original taproom, the brewpub on Logan Square, where I sampled several sours and Mom ordered—wait for it—a vodka sunrise. At the perplexed look of the bartender, she said, “you know, a tequila sunrise … but with vodka instead.” He did as she said, and I laughed but John pointed out that they have a full bar for people like her who aren’t beer drinkers (*shrugs*).

Before we left, John gave us a tour of the behind-the-scenes of the original location. Revolution is one of the 50 biggest craft breweries in the nation, and so the bulk of their production has moved a mile-and-a-half away to North Kedzie Avenue, where there’s also a taproom, but we wanted the full lunch experience, so I also ordered a grilled cheese with short rib, and it did not suck. I’d go back for Revolution’s food and its beer any ol’ day.

After a couple pints for John and me—Mom stuck to her single vodka sunrise, it being 11am on a Thursday and all—John took us on a tour of the neighborhood. There was even more street art than we originally saw, smaller installations side-by-side all throughout the arteries that deviated from North Milwaukee Avenue.

Eating Deep-Dish Pizza

I know, I know, this is something locals would never think of doing as it’s a tourist thing. But guess what? We’re tourists! We had no shame gluttonously digging into a deep-dish pie, then putting on our fat pants and having a night in at the hotel. We initially attempted dinner at the River North location of Gino’s, but they were closed for a private event, so we wound up at Lou Manalti’s instead, and it was great. We ordered a pitcher of sangria, which just meant we were in bed by 8:30pm, ha. Had we wanted to brave rush-hour traffic, we would have gone to Pequod’s Pizza, which industry friends tell me has the actual best deep-dish pizza in Chicago. Ah well, next time!

Sipping Cocktails at the Chicago Athletic Association

My trendy Nashville friends directed me to Cindy’s Rooftop at Chicago Athletic Association Hotel, where we went pre-Hamilton—it’s the perfect place to go before the show given it’s just a five-minute walk, but heed my advice and make a reservation—then wouldn’t you know, we ran into my dear college friend Glenn, who nabbed the seat next to us on the rooftop having no idea it was me. What are the odds? I knew we were in the right place if a local took his colleague there. I also did manage to (finally!) surprise Mom when one of her dear friends Michelle, who moved to Pennsylvania a couple years ago, messaged me that she was now working in Chicago and wanted to meet us for a drink.

On your way back down from Cindy’s, definitely stop and take in the beauty of the lower floors of Chicago Athletic Association Hotel and all its nooks and crannies.

We also went to Three Dots and a Dash the following night with Glenn and sipped on some fun tiki-style cocktails, each of which was served in appropriate barware. I loved this subterranean bar with a speakeasy feel to it; you access it from a alley between blocks that’s lit by tiki torches. I’d also recommend making a reservation, as we were kicked out of our table after an hour and banished to the bar because every table was spoken for (on a Thursday night in late fall, too … go figure!).

And the Main Attraction: Hamilton!

There’s nothing I can possibly add to the commentary of Lin-Manuel Miranda’s game-changing, hip-hop-driven musical that hasn’t already been said, so I’ll just leave it at this: Even if you think you don’t like musicals (AHEM, SVV), you will like Hamilton. It’s fast-paced, it’s fun, it’s emotional, it’s entertaining, it’s educational—I could go on. My only criticism of the cast was that none of the female roles (i.e. the Schuyler sisters) were particularly compelling. The men, however—shoutout, Thomas Jefferson and King George—were phenomenal; some of the funniest performances I’ve seen in my 25 years of Broadway-going.

When I purchased tickets, we could have gotten up as close as the fourth row, but while a musical enthusiast I am, I’m also the daughter of a CPA and I just couldn’t stomach spending $500+ a ticket. Luckily, starting around row Q on the orchestra level, the price dropped significantly to $182 a ticket before fees. We sat in Orchestra C, Row U, at the very end by the aisle. And sure, it would be been nice to be a few more rows closer to the stage, but all in all, I was perfectly happy with our seats. It’s not a huge theater after all. And for those of you thinking $200 a ticket is still highway robbery, there are plenty of seats with obstructed views that cost $72 if you’re willing to make that sacrifice.

I will echo what other people have said and that’s: Go see Hamilton and just sit back and enjoy your inaugural experience, knowing you’re going to miss half of it as the lyrics just move so fast. Then plan a second viewing if you can swing it to actually pick up on all the nuances. That second time will fall this month for my mom and for me in 2020 when the national tour comes to Nashville!

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On the eating front, we had a long list of restaurants to get to—we did get to Beatrix and the Albert, both of which I highly recommend—but my mom eats like a bird and plus we were in a rush much of the trip, so didn’t adopt my normal five-meals-a-day schedule while traveling. Still, I compiled this Chicago restaurants list from foodie friends and social media followers, which is where SVV and I will start whenever we finally make it to the Windy City together:

Love the romp through my neck of the woods! If you do go back to the Hancock and go to the Signature room, go around dusk, and go to the ladies restroom (sorry men). Best view of the city when the lights start coming on. Food wise: Publican (for a meat-centric meal), Maude’s Liquor Bar (for date night French fare), Glenn’s Diner (for seafood), Sun Wah BBQ (for Peking duck meal), and Hoosier Mama (Pie). I could go on and on. If you come in the summer, you can get amazing tacos and a Mexican coke at a street market near the UIC campus. It’s called Maxwell Street Market (its a flea market).

Oh my goodness you did all my favorite Chicago things! My #1 suggestion to visitors is to get a drink at the Signature Lounge (and to visit the ladies’ room if you can–the view is incredible). I’m so glad y’all had a good time!

What a great recap of your trip! So fun to see you guys! I’m excited to visit Revolution soon. Did you hear about the Hancock Signature Room elevator accident a couple of weeks ago? It resulted in the fire department cutting through the wall of the parking garage to rescue the people inside!

I’d say most Broadway shows in the US are $150-$200, unless you get in on the day-of lottery or rush tickets for $25. So the fact that Hamilton tix were in that range in Chicago (vs. in the thousands in NYC) was a deal in my eyes!